I know which of my teenage students smokes weed in the park after class on Fridays, and which other students are with him. I know which ones are struggling with making friends in their first few weeks at college, and which ones aren’t. I know which of my students chafe against overly strict parents on a regular basis. I know which one spends every weekend in the hospital due to a chronic condition. I know which ones got arrested last night.

I know all these things because I follow them all on various social media services. And they know I know; this isn’t some kind of stolen glance into the online life of teenagers that no one is supposed to see. Contrary to popular belief among adults, these teenagers are not oblivious to privacy settings and do care a good amount about who can see what online. If anything, most of them have consciously chosen what they want to show to me and the rest of the world through social media. And what they’re telling us is who they are and what they need from us as mentors.

Are actual teachers—that is, those employed by the school system—tapped into this wealth of information from their students? Likely not. The teachers I know are often discouraged, and sometimes downright forbidden from, interacting with their students on social media. While these policies are in place to help protect both teachers and students from all manner of things, this wall of separation may be keeping teachers from truly knowing their students in a time when teens need a mentor more than ever.

Becoming Techie Teacher

Dan O’Neil and me interacting with students during one of our Civic Innovation Summer sessions.

First, I want to clear the air before I muddle it up again. I am not a professional teacher or instructor. In fact, teaching teenagers is not something I thought I would find myself doing at any point in my life. A lifelong nerd with limited patience, I’ve never considered myself particularly great at teaching other kinds of people—parents, siblings, friends, interns—and I’m painfully awkward with kids. I never planned on having children myself either, meaning I’d carefully constructed my adult life around the pretense that I would never be obligated to teach a young person how to do pretty much anything.

Which is why, when I found myself speaking in front of ~150 teenagers for six weeks this summer, it was unlike anything I’d ever done before. I had just become Editor-at-Large at online tech site Ars Technica, and before that, I’d put in time as a back-end web developer. Teaching wasn’t exactly at the top of my list of experience, but Smart Chicago Collaborative director and Everyblock cofounder Dan O’Neil convinced me to jump on board anyway. He was working on putting together the city’s first “Civic Innovation Summer,” a six-week summer program that would give these kids exposure to technology in ways they weren’t likely to get elsewhere.

But this is Chicago, and these students weren’t the soft, pampered teenagers from suburban high schools that have climbing walls in the gym and multiple symphony orchestras. (I went to a school like that myself—one that has churned out a number of journalists, Silicon Valley execs and engineers, and other talent that is fairly impressive for a public school.) No, our students were mostly Chicago Public School (CPS) kids from all over the city—you know, the ones who are facing school closures and have to rely on a temporary program called “Safe Passage” so they can navigate their way to school through various gang territories. For those who don’t know about Safe Passage, it is an official, CPS-sanctioned program that can barely hold onto its own staff due to shootings along the routes.

One of the goals behind Civic Innovation Summer was, in fact, violence reduction. Keeping wily teenagers off the streets during violent Chicago summers is always a priority for the city. But beyond that, our goal was to expose these kids to the different kinds of people who work in tech, and teach them about the kinds of things they could create in the future with a handful of tech skills. I’ve already written a bit about what we did during Civic Innovation Summer, but one of the things we did that seemed to resonate among students the most was bring in high-profile speakers of all colors, genders, and backgrounds to talk about their lives in technology and how they managed to get there.

This was especially important for students who, by their own admission, had no idea computer programmers could be fun people who actually had personalities and used services like RapGenius. They had no idea that people who grew up in single-parent homes and lived on food stamps could end up running their own startups. They didn’t realize women or people of color were much involved in the industry at all, or that there were plenty of other jobs that take advantage of tech skills, even if you don’t become a programmer.

We had hoped to give them the unique experience of having direct access to tech veterans—people who have been through the trenches, and could help mentor a few more young people into becoming technologists themselves. After a handful of lively talks, the students started following our staff and speakers on Twitter, and we started following them back.

They know more than we do about social media

Advising a council of students dedicated entirely to giving voice to incarcerated youth

The thing we didn’t expect was how much we would learn from the students in return. Going into the program, we figured the students would likely have access to smartphones—Android devices, in particular—but we held the popular opinion that they likely didn’t know a lot about privacy online. We prepared an entire four-hour session so we could go hands-on with the privacy controls on various social networks. We were convinced that students simply hadn’t been fully informed about how to control their privacy, and they would be better off in the electronic world once we showed them how to find the settings.

We were wrong—at least about the not knowing or caring part. What we adults learned during those six weeks was that these teenagers were extremely savvy with privacy on social media, sometimes to the point of bafflement. For example, did you know that many teens “delete” their Facebook accounts altogether every time the rest of us would just log out? They’re taking advantage of the fact that Facebook actually keeps much of your account information on its servers when you decide to “leave” the service, allowing them to stay under the radar from nosy friend, parent, or public searches while they’re not online. Their photos disappear and their status updates go on the down-low—at least until the next time they log back in by re-activating their accounts.

(As someone who had to sneak around her own parents to get online as a teenager, I had to admit to myself: this was genius.)

That’s just one example, but it’s my favorite one. When we tried to walk the students through the privacy settings on Facebook, Twitter, Instagram, and other services, the kids were outright bored. (This was not the case for other sessions I taught, such as one on getting started with HTML. That one ended up being wildly popular, especially among the girls in the class.) Instead, they told us they already knew how to do all those things; their real problems with social media came from password hacks that allowed others to hijack their accounts and be abusive to others while posing as them. The same problem that, let’s be honest, we all face.

I was a bit surprised. I had spent years writing social media privacy articles at Ars Technica for arguably some of the most technically savvy readers on the Internet, and my inbox was constantly bursting with messages from fully-grown adults who had never heard of nearly any privacy settings before. I was used to teaching people how to limit who sees their Facebook posts over and over for years. I had given an entire talk to an auditorium full of techies about how to keep themselves safe and under-the-radar online, and had crowds of people asking me questions afterwards.

I came from a world where everyone believes the kids are the ones who have no clue. Instead, the kids were the ones asking me why any person with a brain would let their phone attach a GPS location to a photograph’s EXIF file. (Public service announcement to The Olds™: you can turn that off.)

Is anyone listening?

Me advising a student in private on how to get better traction for her summer projects on Twitter

Of course, not every single student knew everything there was to know about privacy online. But overall, I came away feeling like inner city high school students knew more about this area of tech than most adults. There is some recent data from the Pew Internet & American Life Project that supports this theory.

Another recent Pew study shows that young adults are the most likely to take privacy-conscious steps online:

The lesson I learned is that they are, in general, quite careful and deliberate about what they post online for all to see. And they know we’re all watching; according to their exit surveys, most students were happy to hand over their Twitter/Instagram/Facebook/SnapChat names, saying they felt comfortable with adults learning more about the realities of their teenage lives.

Those realities were what put these students’ lives into perspective—for me and a number of other adults involved in Civic Innovation Summer.

That student who posts photos of questionable substances to Instagram is the same one who asks the most poignant questions in class—out of hundreds of students, he originally stood out to us because of his participation, as well as the business ideas he came up with during a session we held on startups. He also often goes on Twitter rants against America’s failed drug war and observes the effects of Chicago’s deep segregation on his friends. Sometimes I forget I’m following a teenager when I see his tweets fill my stream.

Another student, quiet and polite in class, revealed via social media that she’s been sleeping in the bathroom at school now that the semester has started—partly because she’s having a hard time making friends, and partly because doesn’t want to face her life at home. We had other students who would arrive hours early for class or stay for hours afterwards because, as they revealed on Twitter, they had nowhere else safe to be during that time.

What they’re telling us is what their lives are like when they’re not sitting in class, obediently scribbling notes or quietly falling asleep in the back. They’re telling us what their struggles are and, perhaps indirectly, what they could use help with in order to make it in one piece to adulthood. But is anyone listening?

Whether our teens will eventually regret the things they post online is the wrong debate to have—or at least, it’s a debate we should have later on. Instead, we should be asking ourselves why we, as a society, discourage the real teachers, counselors, and principals from seeing a full picture of what their students are up to and what can be done to help.

For example, teachers are often restricted from communicating with students over social media thanks to FERPA, which is meant to protect privacy regarding scores or other school-related things on unregulated channels. But teachers are also discouraged from following or interacting in other ways, too—a teacher “caught” following one student on Twitter but not another could be accused of playing favorites when grades come out later.

And teachers themselves are so scared of setting a bad example themselves online that they’re afraid any move they make to see what students are up to could get them fired. A former high school teacher friend of mine told me tales of being banned from posting photos with a drink in her hand—any kind of drink, even if it’s orange juice—because it could be misconstrued as promoting alcoholism, and another story about never talking about dice in any way because it could be seen as promoting gambling. “There are so many things that keep teachers’ hands tied that the risks associated with using social media isn’t worth it to most,” she told me. “Teachers are expected to live up to a standard that is impossible.”

In fact, two other teachers I spoke to from different schools said they faced similar restrictions, especially related to drinks in the hand. (All of the teachers preferred to remain anonymous because they weren’t authorized to discuss school policy.) And keeping those photos out of the public eye won’t necessarily help. Teacher Ashley Payne was forced to resign from her job after posting a photo of her apparently holding a glass of wine—and another with a glass of beer—to her private Facebook page during a trip to Europe, despite the fact that her school had no solid policy on such postings. Years later, her school district has now spelled things out further: teachers are banned from making social network connections with students except under school-sanctioned circumstances.

The result of such policies is a group of adults—those who are largely responsible for our kids’ intellectual development—plugging their ears and yelling “LA LA LA LA” when it comes to students on social media. That is a terrible thing, especially since social media is arguably the number one place we should look when we want to find out how our students are feeling, and where they need help.

Some researchers now argue that high schoolers with an adult mentor means a 50 percent greater likelihood of attending college—disadvantaged students are 100 percent more likely if they have an adult mentor. And that mentor doesn’t even have to do anything special: “Comments from study participants indicate that their mentors weren’t necessarily doing anything extraordinary, just being involved and treating the young person as an important human being,” Brigham Young University sociology professor Lance Erickson wrote of his study published in the journal Sociology of Education.

But only seven percent of disadvantaged students report having a mentoring relationship with a teacher, leaving so much potential on the table to connect with students who need mentors the most. Meanwhile, those students are tapping away on their phones, broadcasting their thoughts to everyone and no one as they try to progress into the next stage of their lives—mostly on their own.

“I just want to die. Please leave me the fuck alone,” tweeted one of my students recently, just before the school year started again. “Somebody to talk to would be nice.”